Gramicidin S

Gramicidin S
Structural formula of Gramicidin S
Ball-and-stick model of the Gramicidin S molecule
Clinical data
Routes of
administration		Topical
Identifiers
  • Gramicidin S
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC60H92N12O10
Molar mass1141.470 g·mol−1
3D model (JSmol)
  • CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)Cc4ccccc4)CC(C)C)CCCN)C(C)C)Cc5ccccc5
  • InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1 checkY
  • Key:IUAYMJGZBVDSGL-XNNAEKOYSA-N checkY
  (verify)

Gramicidin S or Gramicidin Soviet[1] is an antibiotic that is effective against some gram-positive and gram-negative bacteria as well as some fungi.

It is a derivative of gramicidin, produced by the gram-positive bacterium Brevibacillus brevis. Gramicidin S is a cyclodecapeptide, constructed as two identical pentapeptides joined head to tail, formally written as cyclo(-Val-Orn-Leu-D-Phe-Pro-)2. That is to say, it forms a ring structure composed of five different amino acids, each one used twice within the structure.[2] Another interesting point is that it utilizes two amino acids uncommon in peptides: ornithine as well as the atypical stereoisomer of phenylalanine. It is synthesized by gramicidin S synthetase.[3]

  1. ^ Gause GF, Brazhnikova MG (1944). "Gramicidin S and its use in the Treatment of Infected Wounds". Nature. 154 (3918): 703. Bibcode:1944Natur.154..703G. doi:10.1038/154703a0. S2CID 4125407.
  2. ^ Llamas-Saiz AL, Grotenbreg GM, Overhand M, van Raaij MJ (March 2007). "Double-stranded helical twisted beta-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids". Acta Crystallographica. Section D, Biological Crystallography. 63 (Pt 3): 401–7. Bibcode:2007AcCrD..63..401L. doi:10.1107/S0907444906056435. PMID 17327677.
  3. ^ Conti E, Stachelhaus T, Marahiel MA, Brick P (July 1997). "Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S". The EMBO Journal. 16 (14): 4174–83. doi:10.1093/emboj/16.14.4174. PMC 1170043. PMID 9250661.